Three Perfect Days: A trip to Chicago

Before heading out for the day drop your bags at your hotel. We recommend using United Hotels to find the perfect one. Then, it’s time to explore downtown (or “The Loop”). How you do this all depends on what interests you.

Museum and culture lovers

If you love art, history, science, animals, space, or just a museum in general, there’s several museums to choose from, especially in and close to The Loop. If you plan to hit multiple museums, we suggest getting a CITYPASS, or seeing which ones have free days while you’re in town.

The Art Institute of Chicago has a collection spanning thousands of years, from the 12th century to the present day. Works by Vincent van Gogh, Georgia O’Keefe and Salvador Dali are favorites of United employees. But it’s the Thorne Miniature Rooms (which are exactly what they sound like) that many of us have been staring at since we were kids.

A little further south you’ll find several more museums fairly close to each other:

• Explore the universe (and a view of the Chicago skyline) at the Adler Planetarium.
• Take a walk through 4.6 billion years of history (and see the largest discovered T-Rex) at the Field Museum.
• See beluga whales, otters, penguins and other sea critters at the Shedd Aquarium.

You can venture even further south to Hyde Park for the Griffin Museum of Science and Industry, for interactive science exhibits, model trains and more. Head north to the Chicago History Museum in Old Town to learn more about the history of the city.

Sight seers

If your goal is to see as much of downtown as possible, it can be hard to do everything in a day—but this should help narrow it down:

• Millennium Park is part park, part outdoor art exhibit, and part music venue by summer and ice-skating rink by winter. There’s also art installations like Cloud Gate (better known as “The Bean”) and Crown Fountain.
• Roam The Loop in search of more outdoor art, including world-famous sculptures like Flamingo by Alexander Calder, Untitled by Pablo Picasso, and Miró’s Chicago by Joan Miró.
• Explore by water on a Chicago River architecture tour to see more of the city, learn about the city’s history and architecture, and take a ride down the Chicago River.
• Stay on land and take a stroll along the Riverwalk to enjoy views, eateries and bars.
• Shop and dine along the Magnificent Mile (aka “Mag Mile”). This 13-block stretch of Michigan Avenue starts at Oak Street and ends at the Chicago River.
• Take a dip in Lake Michigan with a view of the city at Oak Street Beach.

Foodies

Chicago is a food city. You can find top notch food from all over the world here. While a lot of great food is found in the neighborhoods throughout Chicago, the West Loop has downtown’s best dining. There’s something for every craving and Michelin Bib Gourmand restaurants are plentiful:

• Go to Girl and the Goat for new American cuisine from Top Chef’s Stephanie Izard.
• Rose Mary is a fusion of Italian and Croatian with outdoor seating options.
• If you want a steak, head to Swift & Sons.
• For a taqueria with a casual vibe, Tacombi has you covered.
• For okonomiyaki and other Japanese favorites, head to Gaijin.
• Avec serves up mediterranean small plates at communal tables.

Looking for a Chicago classic? A little north of The Loop, in River North, is Mr. Beef, where you’ll find both the city’s best beef dip sandwich (in my opinion) and the inspiration for The Bear.

Exploring Chicago’s neighborhoods is the only way to see the real city. But, you can’t see them all in one trip, so here are nine that United employees rave about the most.

North side

In nearly every north side neighborhood you’ll see brownstone houses and apartment buildings next to Michelin-starred restaurants and world-renowned museums.

Uptown

Uptown is just off the lake and Lakefront Trail. Here you’ll find Montrose Beach, a favorite of locals and less crowded than other beaches in the city. Plus, it’s close to Montrose Point Bird Sanctuary a 15-acre nature preserve great for birding and hiking.

Asia on Argyle is strip off the Argyle Red Line stop packed with a lot. There’s food from all over Asia, largely Vietnam. A popular spot is Bambu, where the bobaristas whip up fresh dessert drinks and foods. Stay after your meal for shopping, murals and a night market in the summer.

For dinner, I recommend the sambussa sampler and a messob from Demera, an Ethiopian hot spot. For a drink, head to the The Green Mill. While this jazz club is infamous for Al Capone’s favorite booth, it’s also long been the center of Chicago jazz and hosts regular poetry slams.

Lakeview

Lakeview, just south of Uptown, is known for its proximity to the lake, Wrigley Field and Boys Town. If you’re in the area check out a drag show like Drag Brunch at The River.

Movie buffs should go to the Music Box Theatre, which has been around since 1929. They show indie, foreign, and cult classic films. And if there’s room in your suitcase for a little bit of shopping, Lakeview is littered with vintage, thrift and consignment shops. Studio 32 is a local favorite.

Hungry? Here’s what we love to eat in Lakeview:

• Korean fried chicken at Crisp.
• The Chicago Diner’s vegetarian and vegan takes on your diner favorites.
• Craft beer and good food at Corridor Brewery & Provisions.

Lincoln Park

Taking the Lakefront Trail south from Lakeview, you’ll hit Lincoln Park next. The trail leads you right inside the free Lincoln Park Zoo (the flamingos and polar bears are both a personal favorite). The Lincoln Park Conservatory is nearby and free as well, though you’ll need to make a reservation before you go.

If you want to stop for a drink and live music, head over to Kingston Mines, one of Chicago’s many blues clubs. Koko Taylor, Eric Clapton and Mick Jagger have all played there. While you’re in Lincoln Park, you must try:

• Armitage Alehouse, a pub worth the hype if you’re looking to dine in.
• The critically-acclaimed deep dish pizza at Pequod’s Pizza.
• Weiner Circle is a Chicago classic for hot dogs and milkshakes.
• Annette’s Italian Ice, a hidden gem only open from March to November.

West side

Many west side neighborhoods have a trendy yet relaxed vibe. These neighborhoods move at a slower pace than others, but there’s no shortage of night life, food and shopping.

Logan Square

You can’t get to the west side of Chicago from the Lakefront Trail, but it’s close to the Blue Line. If you’d rather walk or bike, The 606 is an abandoned rail line turned paved trail that runs through Logan Square, Humboldt Park, Wicker Park and Bucktown.

Logan Square has great street art. The murals on Milwaukee Ave are ever-changing and quite literally add color to an already vibrant neighborhood. Just west of Milwaukee you’ll also find City Lit Books. Their staff picks section is always on the money.

When you’re ready to eat, you have a lot of options:

• In the morning and early afternoon, Bang Bang Pie & Biscuits serves up sweet and savory pies (and biscuits).
• For Macau comfort food, Noodlebird is the place to go.
• Stop by Superkhana International for Indian food with a Chicago flare.

Wicker Park

Continuing south from Logan Square is Wicker Park, where you’ll find an artsy and bohemian vibe. There are both art galleries and boutiques selling clothes where trendy meets vintage, like Saint Alfred and P45. Myopic Books is a three-story shop with over 80,000 books and regular poetry nights. You could spend an entire afternoon there if you wanted. I have. Plus, there’s the neighborhood’s namesake: Wicker Park with its gardens and fountain.

When your stomach starts growling, you have a lot of options in Wicker Park:

• For ramen and sake, head to Kizuki Ramen.
• At Mott St. you’ll find an umami-filled menu (and, rumor has it, the city’s best burger).
• Lilac Tiger serves up Korean Indian fusion food and cocktails.

Ukrainian Village

Next stop on the west side of town is Ukrainian Village. This is a more relaxed part of the city, but there’s still a lot to do. The Delta M sells both traditional and modern Ukrainian goods, including jewelry, clothes, paintings and more. The Ukrainian Institute of Modern Art features work by some of Ukraine’s most famous artists and the Vertical Gallery often features emerging local artists.

There’s a variety of food in Ukrainian village, including:

• Ann’s Bakery and Deli, a Ukrainian shop selling breads, pastries and sandwiches.
• For Polish favorites, including pierogi, head to Kasia’s Deli.
• Check out Kasama, the first Filipino restaurant to earn a Michelin star.

South side

The south side has defined Chicago’s culture and character for decades.

Chinatown

Heading south from The Loop, Chinatown is just off both the Red Line and Green Line. You can also take the Chicago Water Taxi from downtown. It’s a straight shot west from the Lakefront Trail, if you’re biking or walking.

Chinatown Square is a two-story outdoor mall with all kinds of boutiques and restaurants, including Ichiban Candy and Snacks. If you’re looking for a park you can enjoy with the kids, Ping Tom Memorial Park hosts bamboo gardens and a playground with a trail throughout.

No trip to Chinatown is complete without trying the food. Here are our top picks:

• People from all over the city go to QXY Dumplings for their namesake dish.
• MingHin is a great dim sum spot.
• For soups and Szechuan dishes, head to MCCB Chicago.

Pilsen

Directly west of Chinatown is the Pilsen neighborhood, filled with Latino culture, music, art, nightlife and more. The murals on 16th street are must-see. They’re everywhere, on the front of homes, on overpasses, on train platforms—big, beautiful works of street art seamlessly integrated into the neighborhood.

18th street is one of the coolest streets in the city, with dozens of restaurants, museums and art galleries (including the National Museum of Mexican Art), bookstores and bars. Don’t just take our word for it—Timeout named 18th street one of the coolest streets in the world in 2024.

You’ll find something to eat at these 18th street favorites:

• For something sweet, go to the Panaderia Nuevo Leon bakery.
• 5 Rabanitos Taqueria is a community favorite.
• If you like carnitas and chicharron, Carnitas Uruapan is the place for you.

Hyde Park

A few miles south of Pilsen and Chinatown, right along the Lakefront Trail, is Hyde Park. It’s home to the University of Chicago and it’s three museums. There’s also the grassy Jackson Park. This over 500-acre park includes the gilded bronze Statue of the Republic, the Wooded Island and its Japanese style Osaka Garden, Bobolink Meadow and a vegetable and flower garden. Another popular urban hiking spot is Promontory Point thanks to its proximity to Lake Michigan. If you’re interested in architecture, also check out Frank-Lloyd Wright’s famous Robie House. Lastly, head to Hyde Park Records for vinyl and CDs from a variety of genres and decades.

If you’re looking for the best eats in Hyde Park, we’ve got you covered:

• For a taste of the south, head to Roux.
• The Neopolitan pizza at Nella’s is worth the trip.
• Check out Valois for cafeteria-style restaurant that’s been around since 1921.

Chicago locals know, there’s always something going on. Whether it’s festivals, comedy, concerts, theater or games—you’ll find a live event for any interest year-round.

Sports

Chicago has nearly every major sport covered:

• See the Chicago Cubs play baseball at Wrigley Field (one of only two 100-year-old baseball stadiums in the U.S.), or the Chicago White Sox at Guaranteed Rate Field, best known for its food stands.
• The United Center (also known as the house that Michael Jordan built) is home to our basketball team, the Chicago Bulls, and six-time Stanley Cup winners, the Chicago Black Hawks.
• Our WNBA team, the Chicago Sky, is one of the best in the league and play at the Wintrust Arena.
• The Chicago Bears (one of the oldest football teams in the NFL) and our men’s soccer team, the Chicago Fire, play at Soldier Field.
• See the women’s soccer team, Chicago Red Stars, and our rugby team, Chicago Hounds play at SeatGeek Stadium.

Music

Chicago is known for gospel and house music, as well as blues and modern jazz. We celebrate our strong music scene throughout the city at both seasonal and year-round venues.

In the summer, it’s all about outdoor concerts and music:

• Lollapalooza is at Grant Park in August.
• Millennium Park hosts the Chicago Blues Festival in June, the Chicago Jazz Festival in late August and early September and the Grant Park Music Festival all summer long.
• Pitchfork Music Festival is at Union Park in July.
• Douglass Park hosts Riot Fest in September.

There’s also smaller music venues if that’s more your vibe. The Vic, Lincoln Hall and Salt Shed are all on the north side of the city and places United employees enjoy.

Theater

Chicago is a big theater town—we have Broadway in Chicago and get previews of pre-Broadway plays and musicals. Shows are constantly on rotation, but some of our favorite theaters and companies include:

• Chicago Theatre, a Chicago landmark.
• The nearly 100-year-old Goodman Theatre puts on both original and classic shows.
• The not-for-profit Steppenwolf Theatre is a small space to see a play.
• The lavish Lyric Opera of Chicago is located right on the Chicago River.
• The Joffrey Ballet performs The Nutcracker every winter and other rotating shows throughout the year.
• The Chicago Symphony Orchestra plays at the Symphony Center and is one of the top five orchestras in the country.

Comedy

Whether it’s improv (which was invented at the University of Chicago), stand up or open mic nights, you’ll find a great spot to laugh with your friends, family or partner:

• If you like improv check out Second City, home of Steve Carrell, John Belushi and Bill Murray.
• Both well-known and emerging stand-up comedians perform at the Laugh Factory.
• Lincoln Lodge is a small, non-profit run stand-up comedy club.
• One of Chicago’s original stand-up clubs, Zanies, is also worth a visit.

Festivals

Summer in Chicago is all about festivals. Some are in parks downtown and some block entire neighborhood streets. There’s too many to name them all, but here are a few of our favorites:

• For the best food and drink from the neighborhoods, try Taste of Randolph, Taste of Lincoln, Burger Fest and the Craft Beer Festival.
• Peruse art and go shopping at Northalsted Market Days, Wells Street Art Festival and the Old Town Art Fair.
• In June, check out the Chicago Pride Parade and Chicago Pride Fest.
• Catch a movie outdoors at the Millennium Park Summer Film Series.

Here in the cooler months? No worries.

• In October, Open House Chicago lets you explore some of Chicago’s historical buildings not typically open to the public.
• From November through January, the Zoo Lights are up at the Lincoln Park Zoo, creating a winter wonderland.
• Open from Thanksgiving through December, the Christkindlmarket provides holiday fun, treats and activities both downtown and on the north side.
• Restaurant Week typically takes place around mid-January and lets diners enjoy special prix fixe menus from restaurants around the city and suburbs.

To us at United, Chicago is more than just a homebase for our operations. It’s our hometown. We’re proud of the history, the culture, the sites, the food— and we’re excited to share it with you. See you soon!